US9597270B2 - Hydrogel-forming material - Google Patents
Hydrogel-forming material Download PDFInfo
- Publication number
- US9597270B2 US9597270B2 US14/433,171 US201314433171A US9597270B2 US 9597270 B2 US9597270 B2 US 9597270B2 US 201314433171 A US201314433171 A US 201314433171A US 9597270 B2 US9597270 B2 US 9597270B2
- Authority
- US
- United States
- Prior art keywords
- hydrogel
- group
- forming material
- gly
- minutes
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000000463 material Substances 0.000 title claims abstract description 61
- 239000000017 hydrogel Substances 0.000 claims abstract description 59
- -1 fatty acid salt Chemical class 0.000 claims abstract description 36
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 33
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 28
- 229930195729 fatty acid Natural products 0.000 claims abstract description 28
- 239000000194 fatty acid Substances 0.000 claims abstract description 28
- 150000002632 lipids Chemical class 0.000 claims abstract description 25
- 239000000654 additive Substances 0.000 claims abstract description 22
- 230000000996 additive effect Effects 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 5
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- 125000003277 amino group Chemical group 0.000 claims abstract description 5
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 17
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 claims description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims description 4
- 229940070765 laurate Drugs 0.000 claims description 4
- 229940105132 myristate Drugs 0.000 claims description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 4
- 229940049964 oleate Drugs 0.000 claims description 4
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims description 4
- OYHQOLUKZRVURQ-HZJYTTRNSA-M 9-cis,12-cis-Octadecadienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O OYHQOLUKZRVURQ-HZJYTTRNSA-M 0.000 claims description 3
- YZXBAPSDXZZRGB-DOFZRALJSA-M Arachidonate Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC([O-])=O YZXBAPSDXZZRGB-DOFZRALJSA-M 0.000 claims description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 3
- 229940114078 arachidonate Drugs 0.000 claims description 3
- UKMSUNONTOPOIO-UHFFFAOYSA-M behenate Chemical compound CCCCCCCCCCCCCCCCCCCCCC([O-])=O UKMSUNONTOPOIO-UHFFFAOYSA-M 0.000 claims description 3
- 229940116224 behenate Drugs 0.000 claims description 3
- XMHIUKTWLZUKEX-UHFFFAOYSA-M cerotate Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC([O-])=O XMHIUKTWLZUKEX-UHFFFAOYSA-M 0.000 claims description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 claims description 3
- VZCCETWTMQHEPK-QNEBEIHSSA-M gamma-linolenate Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC([O-])=O VZCCETWTMQHEPK-QNEBEIHSSA-M 0.000 claims description 3
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 claims description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 claims description 3
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 claims description 3
- 229940049918 linoleate Drugs 0.000 claims description 3
- DTOSIQBPPRVQHS-PDBXOOCHSA-M linolenate Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC([O-])=O DTOSIQBPPRVQHS-PDBXOOCHSA-M 0.000 claims description 3
- KEMQGTRYUADPNZ-UHFFFAOYSA-M margarate Chemical compound CCCCCCCCCCCCCCCCC([O-])=O KEMQGTRYUADPNZ-UHFFFAOYSA-M 0.000 claims description 3
- FBUKVWPVBMHYJY-UHFFFAOYSA-M nonanoate Chemical compound CCCCCCCCC([O-])=O FBUKVWPVBMHYJY-UHFFFAOYSA-M 0.000 claims description 3
- UTOPWMOLSKOLTQ-UHFFFAOYSA-M octacosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC([O-])=O UTOPWMOLSKOLTQ-UHFFFAOYSA-M 0.000 claims description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 claims description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N pentadecanoic acid Chemical compound CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 3
- QZZGJDVWLFXDLK-UHFFFAOYSA-M tetracosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC([O-])=O QZZGJDVWLFXDLK-UHFFFAOYSA-M 0.000 claims description 3
- UWHZIFQPPBDJPM-BQYQJAHWSA-N trans-vaccenic acid Chemical compound CCCCCC\C=C\CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-BQYQJAHWSA-N 0.000 claims description 3
- VHOCUJPBKOZGJD-UHFFFAOYSA-N triacontanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O VHOCUJPBKOZGJD-UHFFFAOYSA-N 0.000 claims description 3
- 229940070710 valerate Drugs 0.000 claims description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 37
- 239000000499 gel Substances 0.000 abstract description 35
- 238000003756 stirring Methods 0.000 abstract description 22
- 238000001816 cooling Methods 0.000 abstract description 11
- 238000000034 method Methods 0.000 abstract description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 2
- 238000011156 evaluation Methods 0.000 description 50
- 238000012360 testing method Methods 0.000 description 30
- UWDKDOVZZFPTPS-NRFANRHFSA-N (2s)-2-[[2-(hexadecanoylamino)acetyl]amino]-3-(1h-imidazol-5-yl)propanoic acid Chemical compound CCCCCCCCCCCCCCCC(=O)NCC(=O)N[C@H](C(O)=O)CC1=CN=CN1 UWDKDOVZZFPTPS-NRFANRHFSA-N 0.000 description 29
- 238000010438 heat treatment Methods 0.000 description 28
- 239000000243 solution Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 150000004665 fatty acids Chemical class 0.000 description 7
- 229940045845 sodium myristate Drugs 0.000 description 7
- 229940045870 sodium palmitate Drugs 0.000 description 7
- GGXKEBACDBNFAF-UHFFFAOYSA-M sodium;hexadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCC([O-])=O GGXKEBACDBNFAF-UHFFFAOYSA-M 0.000 description 7
- JUQGWKYSEXPRGL-UHFFFAOYSA-M sodium;tetradecanoate Chemical compound [Na+].CCCCCCCCCCCCCC([O-])=O JUQGWKYSEXPRGL-UHFFFAOYSA-M 0.000 description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002537 cosmetic Substances 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 238000001879 gelation Methods 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 0 [1*]C(=O)NC([2*])C(=O)CC([3*])C(=O)O Chemical compound [1*]C(=O)NC([2*])C(=O)CC([3*])C(=O)O 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229940024606 amino acid Drugs 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 4
- 150000001413 amino acids Chemical group 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 125000003473 lipid group Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000003384 small molecules Chemical class 0.000 description 4
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 4
- 229940082004 sodium laurate Drugs 0.000 description 4
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910021642 ultra pure water Inorganic materials 0.000 description 3
- 239000012498 ultrapure water Substances 0.000 description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 2
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000003910 behenoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- 125000004016 elaidoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])/C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000628 margaroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012567 medical material Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-M palmitoleate Chemical compound CCCCCC\C=C/CCCCCCCC([O-])=O SECPZKHBENQXJG-FPLPWBNLSA-M 0.000 description 2
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 238000001338 self-assembly Methods 0.000 description 2
- 229960005480 sodium caprylate Drugs 0.000 description 2
- UDWXLZLRRVQONG-UHFFFAOYSA-M sodium hexanoate Chemical compound [Na+].CCCCCC([O-])=O UDWXLZLRRVQONG-UHFFFAOYSA-M 0.000 description 2
- BYKRNSHANADUFY-UHFFFAOYSA-M sodium octanoate Chemical compound [Na+].CCCCCCCC([O-])=O BYKRNSHANADUFY-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920001059 synthetic polymer Polymers 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000004474 valine Substances 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 229920000936 Agarose Polymers 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001124 arachidoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 125000005645 linoleyl group Chemical group 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 125000001415 nervonoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical group 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 241001478887 unidentified soil bacteria Species 0.000 description 1
- 125000003847 vaccenoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/42—Proteins; Polypeptides; Degradation products thereof; Derivatives thereof, e.g. albumin, gelatin or zein
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/042—Gels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2250/00—Food ingredients
- A23V2250/54—Proteins
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2250/00—Food ingredients
- A23V2250/54—Proteins
- A23V2250/55—Peptide, protein hydrolysate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/10—General cosmetic use
Definitions
- the C 1-3 alkyl group optionally having a C 1 branched chain means an alkyl group that has a C 1-3 main chain and may have a C 1 branched chain. Specific examples thereof may include a methyl group, an ethyl group, a n-propyl group, an i-propyl group, an i-butyl group, and a sec-butyl group. A methyl group, an i-propyl group, an i-butyl group, and a sec-butyl group are preferred.
- a subject of the present invention is also a hydrogel formed using the hydrogel-forming material described above.
- the fiber When the fiber is formed in water, the fiber forms a three-dimensional network structure and a non-covalent bond between the hydrophilic moiety (peptide moiety) on the fiber surface and an aqueous medium, so that the fiber swells. Thus, the whole aqueous solution is caused to gel to form a hydrogel.
- N-palmitoyl-Gly-His prepared in the Synthesis Example was added so that the concentration of N-palmitoyl-Gly-His was 20 mM and the concentration of each fatty acid sodium (Na) salt was 20 to 1 mM (solvent: ultrapure water) (in Comparative Example 2, a fatty acid sodium salt was not added) in a Mighty vial (No. 3, manufactured by Maruemu corporation).
- the mixture was heated at 100° C. for 60 minutes with dry bath Sahara320 (manufactured by AS ONE Corporation), and it was visually confirmed whether or not dispersion occurred.
- Sahara320 manufactured by AS ONE Corporation
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Birds (AREA)
- Engineering & Computer Science (AREA)
- Dispersion Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Polymers & Plastics (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Colloid Chemistry (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012-221632 | 2012-10-03 | ||
JP2012221632 | 2012-10-03 | ||
PCT/JP2013/076837 WO2014054699A1 (fr) | 2012-10-03 | 2013-10-02 | Matériau de formation d'hydrogel |
Publications (2)
Publication Number | Publication Date |
---|---|
US20150250692A1 US20150250692A1 (en) | 2015-09-10 |
US9597270B2 true US9597270B2 (en) | 2017-03-21 |
Family
ID=50435020
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US14/433,171 Active US9597270B2 (en) | 2012-10-03 | 2013-10-02 | Hydrogel-forming material |
Country Status (6)
Country | Link |
---|---|
US (1) | US9597270B2 (fr) |
EP (1) | EP2905016A4 (fr) |
JP (1) | JP6132107B2 (fr) |
KR (1) | KR102178661B1 (fr) |
CN (1) | CN104780909B (fr) |
WO (1) | WO2014054699A1 (fr) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9598622B2 (en) | 2012-09-25 | 2017-03-21 | Cold Chain Technologies, Inc. | Gel comprising a phase-change material, method of preparing the gel, thermal exchange implement comprising the gel, and method of preparing the thermal exchange implement |
ES2705373T3 (es) | 2013-07-09 | 2019-03-22 | Nissan Chemical Corp | Líquido de dispersión y método para formar un hidrogel |
CN107427440A (zh) * | 2015-01-28 | 2017-12-01 | 国立大学法人九州大学 | 含有脂质肽型化合物的保湿基材 |
WO2016208460A1 (fr) * | 2015-06-24 | 2016-12-29 | 日産化学工業株式会社 | Procédé d'ajustement de dureté de matériau de base en bâtonnet comprenant un composé peptide lipidique |
Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0853693A (ja) | 1994-06-07 | 1996-02-27 | Ajinomoto Co Inc | 洗浄剤組成物 |
WO2009005152A1 (fr) | 2007-07-05 | 2009-01-08 | Nissan Chemical Industries, Ltd. | Nouvel agent de formation d'hydrogel sur la base de lipide-tripeptide et hydrogel |
WO2009005151A1 (fr) | 2007-07-05 | 2009-01-08 | Nissan Chemical Industries, Ltd. | Nouveau lipide-peptide et hydrogel |
WO2010106981A1 (fr) | 2009-03-16 | 2010-09-23 | 日産化学工業株式会社 | Matériau de base pour pulvérisation comprenant un agent gélifiant de faible poids moléculaire |
WO2011052613A1 (fr) | 2009-10-26 | 2011-05-05 | 日産化学工業株式会社 | Préparation cosmétique et externe pour la peau, et instrument médical |
WO2012063947A1 (fr) | 2010-11-12 | 2012-05-18 | 日産化学工業株式会社 | Feuille de gel comprenant un agent gélifiant de type peptide lipidique et composé polymère |
WO2012133787A1 (fr) | 2011-03-31 | 2012-10-04 | 日産化学工業株式会社 | Procédé de production de cosmétique, procédé de préparation de gel pour cosmétique, et procédé de réduction de la quantité d'épaississant de masse moléculaire élevée ajouté à des produits de départs de cosmétique |
WO2012144609A1 (fr) | 2011-04-22 | 2012-10-26 | 日産化学工業株式会社 | Matière formant un hydrogel |
CN104582826A (zh) | 2012-06-25 | 2015-04-29 | 日产化学工业株式会社 | 分散液及水凝胶形成方法 |
US20150250880A1 (en) * | 2012-10-03 | 2015-09-10 | Nissan Chemical Industries, Ltd. | Hydrogel-forming material, premix, and hydrogel formation method |
US9265833B2 (en) * | 2008-08-01 | 2016-02-23 | Nissan Chemical Industries, Ltd. | Lipid dipeptide and gel |
US20160129119A1 (en) * | 2013-07-09 | 2016-05-12 | Nissan Chemical Industries, Ltd. | Dispersion and method for forming hydrogel |
-
2013
- 2013-10-02 CN CN201380059210.1A patent/CN104780909B/zh active Active
- 2013-10-02 JP JP2014539789A patent/JP6132107B2/ja active Active
- 2013-10-02 EP EP13843933.6A patent/EP2905016A4/fr not_active Withdrawn
- 2013-10-02 WO PCT/JP2013/076837 patent/WO2014054699A1/fr active Application Filing
- 2013-10-02 KR KR1020157011548A patent/KR102178661B1/ko active IP Right Grant
- 2013-10-02 US US14/433,171 patent/US9597270B2/en active Active
Patent Citations (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0853693A (ja) | 1994-06-07 | 1996-02-27 | Ajinomoto Co Inc | 洗浄剤組成物 |
WO2009005152A1 (fr) | 2007-07-05 | 2009-01-08 | Nissan Chemical Industries, Ltd. | Nouvel agent de formation d'hydrogel sur la base de lipide-tripeptide et hydrogel |
WO2009005151A1 (fr) | 2007-07-05 | 2009-01-08 | Nissan Chemical Industries, Ltd. | Nouveau lipide-peptide et hydrogel |
US8916682B2 (en) * | 2007-07-05 | 2014-12-23 | Nissan Chemical Industries, Ltd. | Lipid peptide and hydrogel |
US8816049B2 (en) * | 2007-07-05 | 2014-08-26 | Nissan Chemical Industries, Ltd. | Lipid peptide and hydrogel |
US8716248B2 (en) * | 2007-07-05 | 2014-05-06 | Nissan Chemical Industries, Ltd. | Lipid tripeptide-based hydrogelator and hydrogel |
US8486896B2 (en) * | 2007-07-05 | 2013-07-16 | Nissan Chemical Industries, Ltd. | Lipid tripeptide-based hydrogelator and hydrogel |
US9289496B2 (en) * | 2008-08-01 | 2016-03-22 | Nissan Chemical Industries, Ltd. | Lipid dipeptide and gel |
US9265833B2 (en) * | 2008-08-01 | 2016-02-23 | Nissan Chemical Industries, Ltd. | Lipid dipeptide and gel |
US9333158B2 (en) * | 2009-03-16 | 2016-05-10 | Nissan Chemical Industries, Ltd. | Spray base material including low-molecular gelator |
US20120035108A1 (en) | 2009-03-16 | 2012-02-09 | Kyushu University | Spray base material including low-molecular gelator |
WO2010106981A1 (fr) | 2009-03-16 | 2010-09-23 | 日産化学工業株式会社 | Matériau de base pour pulvérisation comprenant un agent gélifiant de faible poids moléculaire |
US20120258059A1 (en) | 2009-10-26 | 2012-10-11 | Nissan Chemical Industries, Ltd. | Cosmetic, external skin preparation, and medical instrument |
US20130084305A1 (en) * | 2009-10-26 | 2013-04-04 | Kyushu University, National University Corporation | Cosmetic, external skin preparation, and medical instrument |
US8999300B2 (en) * | 2009-10-26 | 2015-04-07 | Nissan Chemical Industries Ltd. | Cosmetic, external skin preparation, and medical instrument |
CN102596164A (zh) | 2009-10-26 | 2012-07-18 | 日产化学工业株式会社 | 化妆料、皮肤外用剂、以及医疗用仪器 |
WO2011052613A1 (fr) | 2009-10-26 | 2011-05-05 | 日産化学工業株式会社 | Préparation cosmétique et externe pour la peau, et instrument médical |
WO2012063947A1 (fr) | 2010-11-12 | 2012-05-18 | 日産化学工業株式会社 | Feuille de gel comprenant un agent gélifiant de type peptide lipidique et composé polymère |
US20140113976A1 (en) * | 2011-03-31 | 2014-04-24 | Nissan Chemical Industries, Ltd. | Production method of cosmetic, preparation method of gel for cosmetics, and method of reducing use amount of polymer thickener blended in cosmetic raw materials |
WO2012133787A1 (fr) | 2011-03-31 | 2012-10-04 | 日産化学工業株式会社 | Procédé de production de cosmétique, procédé de préparation de gel pour cosmétique, et procédé de réduction de la quantité d'épaississant de masse moléculaire élevée ajouté à des produits de départs de cosmétique |
WO2012144609A1 (fr) | 2011-04-22 | 2012-10-26 | 日産化学工業株式会社 | Matière formant un hydrogel |
US9328137B2 (en) * | 2011-04-22 | 2016-05-03 | Nissan Chemical Industries, Ltd. | Hydrogel-forming material |
CN104582826A (zh) | 2012-06-25 | 2015-04-29 | 日产化学工业株式会社 | 分散液及水凝胶形成方法 |
US20150202586A1 (en) * | 2012-06-25 | 2015-07-23 | Nissan Chemical Industries, Ltd. | Dispersion and method for forming hydrogel |
US20150250880A1 (en) * | 2012-10-03 | 2015-09-10 | Nissan Chemical Industries, Ltd. | Hydrogel-forming material, premix, and hydrogel formation method |
US20160129119A1 (en) * | 2013-07-09 | 2016-05-12 | Nissan Chemical Industries, Ltd. | Dispersion and method for forming hydrogel |
Non-Patent Citations (9)
Title |
---|
Hamachi et al., "Solid Phase Lipid Synthesis (SPLS) for Construction of an Artificial Glycolipid Library," Chem. Commun., 2000, pp. 1281-1282. |
Hamachi et al., "Solid-Phase Lipid Synthesis (SPLS)-2: Incidental Discovery of Organogelators Based on Artificial Glycolipids," Tetrahedron Letters, 2001, vol. 42, pp. 6141-6145. |
Jan. 7, 2014 International Search Report issued in International Application No. PCT/JP2013/076837. |
Jan. 7, 2014 Written Opinion issued in International Application No. PCT/JP2013/076837. |
Jung et al., "Self-Assembly of a Sugar-Based Gelator in Water: Its Remarkable Diversity in Gelation Ability and Aggregate Structure," Langmuir, vol. 17, 2001, pp. 7299-7232. |
Matsuzawa et al., "Assembly and Photoinduced Organization of Mono- and Oligopeptide Molecules Containing an Azobenzene Moiety," Adv. Funct. Mater., 2007, vol. 17, No. 9, pp. 1507-1514. |
Nov. 30, 2016 Office Action issued in Chinese Patent Application No. 201380059210.1. |
Suzuki et al., "Supramolecular Hydrogels Formed by L-Lysine Derivatives," Chemistry Letters, 2004, vol. 33, No. 11, pp. 1496-1497. |
Suzuki et al., "Supramoledular Hydrogel Formed by Glucoheptonamide of L-Lysine: Simple Preparation and Excellent Hydrogelation Ability," Tetrahedron, 2007, vol. 63, pp. 7302-7308. |
Also Published As
Publication number | Publication date |
---|---|
CN104780909A (zh) | 2015-07-15 |
JPWO2014054699A1 (ja) | 2016-08-25 |
JP6132107B2 (ja) | 2017-05-24 |
KR102178661B1 (ko) | 2020-11-13 |
EP2905016A4 (fr) | 2016-04-06 |
CN104780909B (zh) | 2018-02-13 |
US20150250692A1 (en) | 2015-09-10 |
EP2905016A1 (fr) | 2015-08-12 |
KR20150063151A (ko) | 2015-06-08 |
WO2014054699A1 (fr) | 2014-04-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6065245B2 (ja) | 新規ジペプチド並びにゲル | |
KR101963441B1 (ko) | 하이드로겔 형성 재료 | |
JP5388848B2 (ja) | 新規脂質トリペプチド性ヒドロゲル化剤及びヒドロゲル | |
JP5441693B2 (ja) | 新規脂質ペプチド並びにヒドロゲル | |
US9597270B2 (en) | Hydrogel-forming material | |
EP2664321B1 (fr) | Instrument et préparation médicaux comprenant un peptide lipidique et de la gomme arabique | |
Tomasini et al. | Peptides and peptidomimetics that behave as low molecular weight gelators | |
TW403653B (en) | Dry compositions | |
CN110066315B (zh) | 一种新型水凝胶及其制备方法 | |
WO2016088712A1 (fr) | Matériau formant un hydrogel | |
TW201446324A (zh) | 綠色環保多功能胺基酸型界面活性劑、其製備方法及應用 | |
WO2018221445A1 (fr) | Agent gélifiant | |
Pitkäranta | Synthesis and study of two hydrogelators derived from L-Valine |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: NISSAN CHEMICAL INDUSTRIES, LTD., JAPAN Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:MATSUMOTO, KEIGO;REEL/FRAME:035570/0783 Effective date: 20150420 |
|
STCF | Information on status: patent grant |
Free format text: PATENTED CASE |
|
MAFP | Maintenance fee payment |
Free format text: PAYMENT OF MAINTENANCE FEE, 4TH YEAR, LARGE ENTITY (ORIGINAL EVENT CODE: M1551); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY Year of fee payment: 4 |